Hydrochloric Acid → HCID 20535083, compound

HRID 1680930Notes

Reaction equation

HRID 1680930 reaction equation
[NH2:1][C:2]1[N:7]2[O:8][C:9](=[O:11])[N:10]=[C:6]2[N:5]=[C:4]([N:12]([CH2:16][CH:17]=[CH2:18])[CH2:13][CH:14]=[CH2:15])[N:3]=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>O.C(Cl)Cl.C(N(CC)CC)C>[CH2:13]([N:12]([CH2:16][CH:17]=[CH2:18])[C:4]1[N:3]=[C:2]([NH:1][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:7]2[O:8][C:9](=[O:11])[N:10]=[C:6]2[N:5]=1)[CH:14]=[CH2:15]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 20535125HCID 20535125, compound

Product 1

HCID 20535083HCID 20535083, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

7.0 g. of 7-amino-5-diallylamino-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-2-one are suspended in 250 ml. of methylene chloride and 10 ml. of triethylamine, cooled while stirring to 0° C. and treated with 4.5 ml. of benzoyl chloride in 35 ml. of methylene chloride. The mixture is subsequently stirred at 0° C. for 1 hour, then diluted with water and adjusted to pH 4 with hydrochloric acid. The two phases are separated and the aqueous phase is extracted twice with methylene chloride. The organic extracts are combined, dried over magnesium sulfate and evaporated at 20° C. under reduced pressure. The residue is recrystallized from methylene chloride and diethyl ether, there being obtained pure N-{5-diallylamino-2-oxo-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-7-yl}benzamide having a melting point of 182°-183° C.

Workup

  1. additiontreated with 4.5 ml
  2. stirringThe mixture is subsequently stirred at 0° C. for 1 hour
  3. customThe two phases are separated
  4. extractionthe aqueous phase is extracted twice with methylene chloride
  5. dry with materialdried over magnesium sulfate
  6. customevaporated at 20° C. under reduced pressure
  7. customThe residue is recrystallized from methylene chloride and diethyl ether, there

Sources & evidence

ORD record
ord-2210546c9aae415dacc190c37e51d451
Source dataset
uspto-grants-1981_06
Patent number
US04276417

Reaction notes

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